1. Field of the Invention
The present invention is directed to novel substituted-cyclopropyl sulfones. More specifically, in addition to having a sulfonyl ##STR1## group on the ring, the compounds of this invention have a vinyl or ethyl group substituted in the 2-position and an acyl moiety or nitrile or radical derived therefrom present with the sulfonyl group in the 1-position. The sulfones of this invention are useful chemical intermediates and undergo anionic or radical polymerizations.
2. Discussion of the Prior Art
The polymerization of 1,1-disubstituted 2-vinylcyclopropanes has been documented by Iwhan Cho and co-workers (see Journal of Polymer Science, Vol. 17, 3169-3182(1979); Vol. 17, 3183-3191(1979); Vol. 18, 3053-3057(1980); and Polymer Letters Edition, Vol. 18(9), 639-42(1980)). In addition to radical initiated 1,5-type polymerizations, it was also observed that anionic polymerization can be accomplished with such compounds via ring-opening and without participation of the vinyl group. It is thus possible to achieve reactive polymeric materials having a vinyl group and nitrile or ester moiety pendant to the polymer chain.
In view of the desirable properties generally attributed to the presence of sulfonyl groups in polymeric materials, it would be highly desirable and advantageous to have a reactive cyclopropyl monomer bearing such substituents which could be readily polymerized under anionic or radical conditions in accordance with the prior art teachings. However, the preparation of such compounds has heretofore not been possible in view of the limitations of the condensation procedures typically used to prepare cyclopropane derivatives. While E. V. Dehmlow report the preparation of a cyclopropane compound having a sulfonyl group substituted thereon via a carbene insertion reaction (Angew Chem. Internat. Edit., Vol. 13, No. 3, 170-179(1974)), the reaction is not suitable for the preparation of vinyl substituted cyclopropane sulfones.